The first entry to pyrrolo[2,3- c ]quinoline-2,4(3a H ,5 H )-diones

Citation data:

Tetrahedron, ISSN: 0040-4020, Vol: 64, Issue: 19, Page: 4387-4402

Publication Year:
2008
Usage 902
Abstract Views 891
Downloads 10
Link-outs 1
Captures 89
Readers 88
Exports-Saves 1
Mentions 1
Blog Mentions 1
Citations 86
Citation Indexes 86
Repository URL:
http://publikace.k.utb.cz/handle/10563/1000871; http://publikace.k.utb.cz/handle/10563/1000952; http://hdl.handle.net/10563/1000952; http://hdl.handle.net/10563/1000871
DOI:
10.1016/j.tet.2008.02.063; 10.1016/j.carbpol.2007.07.001
Author(s):
Kafka, Stanislav; Klásek, Antonín; Polis, Jiří; Rosenbreierová, Veronika; Palík, Ctirad; Mrkvička, Vladimír; Košmrlj, Janez
Publisher(s):
Elsevier BV; Pergamon Elsevier Science Ltd.
Tags:
Materials Science; Chemistry; Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; pyrrolo[2,3-c]chinolony; chinolinony; Wittigova olefinace; mechanismus; NMR; Pyrrolo[2,3-c]quinolones; Quinolinones; Wittig olefination; Mechanism; vyfukování; mechanické vlastnosti; plasikátor; škrob; termoplastický škrob; film blowing; mechanical properties; plasticizer; starch; thermoplastic starch
Most Recent Blog Mention
article description
Wittig olefination of 3-aminoquinoline-2,4(1 H,3 H )-diones 1 with ethyl (triphenylphosphoranylidene)acetate (Ph 3 P CHCO 2 Et) afforded ( E )-3-amino-4-ethoxycarbonylmethylene-1,2,3,4-tetrahydro-2-quinolones ( E )- 2 and pyrrolo[2,3- c ]quinoline-2,4(3a H,5 H )-diones 3. An alternative approach for the synthesis of 3 via 3-bromoacetamidoquinoline-2,4(1 H,3 H )-diones 7, their corresponding triphenylphosphonium salts 8, and ylides A that undergo intramolecular Wittig reaction, was investigated. Under the applied reaction conditions, the phosphonium salts 8 and ylides A are so unstable that they partly decompose to 3-acetamidoquinoline-2,4(1 H,3 H )-diones 9 during the synthesis of 3.